Dimethyl Sulfoxide → HCID 22638715, compound

Participants

Reaction Steps

Anhydrous DMSO (0.20 mL, 2.8 mmol) was added dropwise to a solution of oxalyl chloride (0.21 mL, 2.4 mmol) in 20 mL anhydrous CH2Cl2 under N2 at −78° C. and stirred for 30 min. A solution of 3-(2-hydroxymethyl-cyclopropyl)-1-(toluene-4-sulfonyl)-1H-indazole-5-carbonitrile (634 mg, 1.63 mmol) in 20 mL anhydrous CH2Cl2 was then added and stirring continued for 40 min. at −78° C. Et3N (1.25 mL, 8.98 mmol) was added and stirring continued for 10 min at −78° C. The reaction was warmed to room temperature and 25 mL water was added. The layers were partitioned, and the aqueous layer was extracted with CH2Cl2. The organic layers were pooled, extracted with brine, and dried over MgSO4, and concentrated in vacuo to give 3-(2-formyl-cyclopropyl)-1-(toluene-4-sulfonyl)-1H-indazole-5-carbonitrile (637 mg, 100%). 1H NMR (500 MHz, CDCl3) 9.54 (1H, d, J=3.66 Hz), 8.20 (1H, d, J=8.85 Hz), 8.05 (1H, s), 7.83 (2H, d, J=8.24 Hz), 7.77 (1H, dd, J=8.85, 1.53 Hz), 7.29 (2H, d, J=8.24 Hz), 2.82 (1H, m), 2.62(1H, m), 2.39 (3H, s), 1.82 (2H, m).

Provenance & Evidence